Imidazole → 3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one

HRID 656602Notes

Reaction equation

HRID 656602 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CN(C=O)C.C(OCC)C>[Si:13]([O:1][CH:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 545831alpha-Hydroxy-gamma-butyrolactone

Product 1

HCID 50462413-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxydihydrofuran-2(3H)-one (5 g, 49 mmol) in anhydrous DMF (50 mL) was added imidazole (6.7 g, 98 mmol) and TBDMS chloride (8.1 g, 54 mmol). The reaction was allowed to stir under an N2 atmosphere at room temperature overnight. The reaction was diluted with diethyl ether and washed with 1 N aqueous HCl×2 then brine×1. The organic phase was dried over Na2SO4 and the solvent removed in vacuo to yield 3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one (11 g, 49 mmol) as a clear oil. [M+H] calc'd for C10H20O3Si, 217. found, 217.

Workup

  1. washwashed with 1 N aqueous HCl×2
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6f7c5d92eaf6472faade91711c2b30bb
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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